An alternative enzymatic route to the ergogenic ketone body ester (R)-3-hydroxybutyl (r)-3-hydroxybutyrate
Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate has been produced thro...
Published in: | Catalysts |
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Main Authors: | , , , , , , |
Other Authors: | , , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2021
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Subjects: | |
Online Access: | https://hdl.handle.net/11392/2448437 https://doi.org/10.3390/catal11010140 https://www.mdpi.com/2073-4344/11/1/140 |
Summary: | Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate has been produced through the transesterification of racemic ethyl 3-hydroxybutyrate with (R)-1,3-butanediol by exploiting the selectivity of Candida antarctica lipase B (CAL-B). The needed (R)-1,3-butanediol was in turn obtained from the kinetic resolution of the racemate achieved by acetylation with vinyl acetate, also in this case, thanks to the enantioselectivity of the CAL-B used as catalyst. Finally, the stereochemical inversion of the unreacted (S) enantiomers of the ethyl 3-hydroxybutyate and 1,3-butanediol accomplished by known procedure allowed to increase the overall yield of the synthetic pathway by incorporating up to 70% of the starting racemic reagents into the final product. |
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